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Cheap flights from Chicago Midway Airport to San José from $185

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to San José

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
16h 15m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:37 pm - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 17m1 stop Atlanta Hartsfield-Jackson
$378Delta
Mon, Nov 16 - Mon, Nov 23
Delta Logo
1:05 pm - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
9h 10m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 4:18 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 18m1 stop Atlanta Hartsfield-Jackson
$378Delta
Wed, Nov 11 - Wed, Nov 18
Delta Logo
11:27 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
10h 48m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:37 pm - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
8h 17m1 stop Atlanta Hartsfield-Jackson
$378Delta
Wed, Nov 11 - Sat, Nov 21
Delta Logo
1:05 pm - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
9h 10m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 10:54 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
15h 54m1 stop Atlanta Hartsfield-Jackson
$378Delta
Wed, Nov 11 - Tue, Nov 17
Delta Logo
11:27 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
10h 48m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 9:42 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
26h 42m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
$383Delta
Wed, Nov 11 - Thu, Nov 19
Delta Logo
11:27 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
10h 48m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:37 pm - 9:42 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
19h 05m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
$383Delta
Wed, Nov 11 - Tue, Nov 17
Delta Logo
6:00 am - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
16h 15m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:37 pm - 12:51 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
22h 14m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
$383Delta
Mon, Nov 16 - Mon, Nov 23
Delta Logo
1:05 pm - 10:15 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
9h 10m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 9:42 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
26h 42m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
$383Delta
Mon, Nov 16 - Tue, Nov 24
Southwest Logo
5:15 am - 12:20 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
7h 05m1 stop Houston Hobby
Southwest Logo
1:20 pm - 10:55 pmSJO  San José Juan Santamaria Intl-MDW Chicago Midway
9h 35m1 stop Orlando
$427Southwest
Sun, Nov 1 - Thu, Nov 5
Southwest Logo
5:15 am - 12:20 pmMDW  Chicago Midway-SJO San José Juan Santamaria Intl
7h 05m1 stop Houston Hobby
Southwest Logo
1:20 pm - 12:05 amSJO  San José Juan Santamaria Intl-MDW Chicago Midway
10h 45m2 stops Orlando Nashville Intl
$431Southwest
Sun, Nov 1 - Thu, Nov 5

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Southwest flights from Chicago Midway Airport to San José

Our best Southwest deals on Chicago Midway Airport to San José flight tickets
Southwest
Nov 1
MDW5:15 amChicago Midway
7h 05m
1 stop
SJO12:20 pmSan José Juan Santamaria Intl
Nov 5
SJO1:20 pmSan José Juan Santamaria Intl
9h 35m
1 stop
MDW10:55 pmChicago Midway
$427
Southwest
Nov 1
MDW5:15 amChicago Midway
7h 05m
1 stop
SJO12:20 pmSan José Juan Santamaria Intl
Nov 5
SJO1:20 pmSan José Juan Santamaria Intl
10h 45m
2 stops
MDW12:05 amChicago Midway
$431
Southwest
Oct 22
MDW11:50 amChicago Midway
8h 50m
1 stop
SJO7:40 pmSan José Juan Santamaria Intl
Oct 29
SJO9:00 amSan José Juan Santamaria Intl
10h 10m
2 stops
MDW8:10 pmChicago Midway
$444

Delta flights from Chicago Midway Airport to San José

Our best Delta deals on Chicago Midway Airport to San José flight tickets
Delta
Nov 11
MDW1:05 pmChicago Midway
9h 10m
1 stop
SJO10:15 pmSan José Juan Santamaria Intl
Nov 18
SJO7:00 amSan José Juan Santamaria Intl
9h 18m
1 stop
MDW4:18 pmChicago Midway
$378
Delta
Nov 11
MDW11:27 amChicago Midway
10h 48m
1 stop
SJO10:15 pmSan José Juan Santamaria Intl
Nov 16
SJO7:00 amSan José Juan Santamaria Intl
26h 42m
2 stops
MDW9:42 amChicago Midway
$383
Delta
Nov 11
MDW11:27 amChicago Midway
10h 48m
1 stop
SJO10:15 pmSan José Juan Santamaria Intl
Nov 16
SJO7:00 amSan José Juan Santamaria Intl
15h 54m
1 stop
MDW10:54 pmChicago Midway
$395

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago Midway Airport to San José that are best for you.

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Route

Depart

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Price

Cheapest round-trip

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Mon 11/16

6:00 am-10:15 pm

1 stop16h 15m

San José Juan Santamaria Intl

Mon 11/23

2:37 pm-10:54 pm

1 stop8h 17m

$378

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Wed 11/11

1:05 pm-10:15 pm

1 stop9h 10m

San José Juan Santamaria Intl

Wed 11/18

7:00 am-4:18 pm

1 stop9h 18m

$378

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Wed 11/11

11:27 am-10:15 pm

1 stop10h 48m

San José Juan Santamaria Intl

Sat 11/21

2:37 pm-10:54 pm

1 stop8h 17m

$378

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Wed 11/11

1:05 pm-10:15 pm

1 stop9h 10m

San José Juan Santamaria Intl

Tue 11/17

7:00 am-10:54 pm

1 stop15h 54m

$378

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Wed 11/11

11:27 am-10:15 pm

1 stop10h 48m

San José Juan Santamaria Intl

Thu 11/19

7:00 am-9:42 am

2 stops26h 42m

$383

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Wed 11/11

11:27 am-10:15 pm

1 stop10h 48m

San José Juan Santamaria Intl

Tue 11/17

2:37 pm-9:42 am

2 stops19h 05m

$383

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Mon 11/16

6:00 am-10:15 pm

1 stop16h 15m

San José Juan Santamaria Intl

Mon 11/23

2:37 pm-12:51 pm

2 stops22h 14m

$383

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Mon 11/16

1:05 pm-10:15 pm

1 stop9h 10m

San José Juan Santamaria Intl

Tue 11/24

7:00 am-9:42 am

2 stops26h 42m

$383
Quickest round-trip

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Sun 11/1

5:15 am-12:20 pm

1 stop7h 05m

San José Juan Santamaria Intl

Thu 11/5

1:20 pm-10:55 pm

1 stop9h 35m

$427

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Sun 11/1

5:15 am-12:20 pm

1 stop7h 05m

San José Juan Santamaria Intl

Thu 11/5

1:20 pm-12:05 am

2 stops10h 45m

$431

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to San José from

How to get the cheapest flight ticket from Chicago Midway Airport to San José

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to San José?

On average, the least expensive day to fly to San José from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $517. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago Midway Airport to San José on a Saturday will generally be more expensive and average around $714. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to San José?

Our data shows that the cheapest Chicago Midway Airport to San José flights are usually those with departure times in the afternoon. Our users have found flights to San José in the afternoon for as low as $512. Flights at noon are often more expensive with an average ticket price of $689.

Can stopping save me money on Chicago Midway Airport to San José flights?

You could potentially save up to 1% on your flight if you consider stops on a Chicago Midway Airport to San José flight.

When to book flights from Chicago Midway Airport to San José

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San José according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San José (MDW to SJO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San José

Best Price Found

$185

Fastest flight time

6h 45m

Direct flights

None
The best one-way flight to San José from Chicago Midway Airport in the past 72 hours is $185. The best round-trip flight deal from Chicago Midway Airport to San José found on momondo in the last 72 hours is $378.
The fastest flight from Chicago Midway Airport to San José takes 6h 45m
There are no direct flights from Chicago Midway Airport to San José. There are no popular flight routes from Chicago Midway Airport to San José.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to San José

  • How far is Chicago Midway to San José Juan Santamaria Intl by plane?

    A flight from Chicago Midway to San José Juan Santamaria Intl will travel around 2210.5 mi. Typically, this will take 6h 45m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    Prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San José Juan Santamaria Intl Airport.

  • What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?

    The travel and health documents you'll need for your trip to San José Juan Santamaria Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San José Juan Santamaria Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago Midway Airport to San José?

Best airlines flying from Chicago Midway Airport to San José

Compare and see reviews for airlines that fly from Chicago Midway Airport to San José with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $503Free CancellationRating
8.0
4,199 reviews
Search Southwest flights

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Jacó
Monteverde
Alajuela
Heredia
Santa Elena
San Gerardo de Dota
Dominical
Esterillos Este

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José?

Finding the right flight to San José from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San José quick and easy, saving you time and money.

Can I find flights from Chicago to San José with flexible booking policies on momondo?

All flight searches from Chicago to San José on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to San José?

momondo provides multiple filters to help you find the best flight to San José from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to San José right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to San José flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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